The PRS-500 USB drivers only work on 32-bit Windows. So if what you use now is 64-bit Windows, forget it.
We had a 500 that I traded back to Sony for $50 and I used the $50 to get a T1 as a gift when it was on sale for $99. That really cut the price.
But to be honest, I would call Sony and tell them you have a 500 that you want to have upgraded. I think Sony won't do it and might give you a discount on a refurbished T2.
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